It’s not clear if Woodside left Motorola voluntarily, although his new role is certainly noteworthy; at Dropbox he will serve as the company’s first chief operating officer.

Woodside’s performance at Motorola further complicates this move. While his Moto X initiative received moderate praise, Woodside failed to steer the company to profitability — despite cutting prices across the board.

Now a Dropbox chief, Woodside faces a difficult task: He must help CEO Drew Houston expand rapidly into enterprise and mobile under the weight of gargantuan expectations.